The research will proceed in four areas. (1) New Approaches to the synthesis of penicillin and penicillin analogs will be studied including a novel intramolecular rearrangement of a 2-aminothiapyran-4-one and a transannular diradical coupling from a thiaazepin. (2) The synthetic methodology developed in the total synthesis of cephalotaxine will be applied to the preparation of 11-hydroxycephalotaxine and drupacine, and elaborated to determine the scope of these methods in natural product synthesis. (3) Electrochemical reduction of organic halides will be applied to the synthesis of a naturally occurring cumulene derivative, and to the generation of reactive anions for organic synthesis. In these studies the mild conditions and selectivity of controlled potential electrolysis will be crucial. (4) The total synthesis of two important natural products, fomannosin and frenolicin will be undertaken.